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Method of synthesizing higher-molecular alcohol

a high molecular alcohol and ethanol technology, applied in the field of high molecular alcohol production from ethanol, can solve the problems of unpreferable oxo method in view of environmental conservation, unfavorable oxo method, and poor profitability, and achieve the effect of efficient collection through clean processes

Active Publication Date: 2011-12-20
SANGI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

"The present invention provides a method for efficiently collecting high molecular alcohols using ethanol as a raw material, with the use of a calcium phosphate-based catalyst for a contact time of 0.4 seconds or longer. This method results in the production of high molecular alcohols with a lower cost and reduced safety management requirements. The method is also environmentally friendly and produces less carbon dioxide as a by-product. The ratio of synthesis of different high molecular alcohols can be controlled by adjusting the contact time. The invention provides a disclaimer of any previously known product, process, or method that does not meet the written description and enablement requirements of the USPTO or EPO."

Problems solved by technology

However, as crude oil prices exceeded 50 dollars / barrel in 2004, and the soaring prices of propylene as a raw material led to the rising production cost of high molecular alcohols, the result is a worsened profitability.
The oxo method necessitates the use of deadly carbon monoxide as a raw material in addition to propylene, and the method comprises a complicated, high-pressure reaction which contributes to the rising production costs.
Furthermore, the oxo method is unpreferable in view of environmental conservation.
However, they are not industrially suitable because of their low selectivity.
WO 99 / 38822 relates to a method for synthesizing 1-butanol with the use of calcium phosphate-based catalysts, although this synthesis method features disadvantages which are associated with the high reaction temperature (as high as 350 to 450° C.) that is involved.
For instance, the selectivity of 1-butanol is low; the catalyst regeneration treatment has to be repeated frequently because of the rapid degradation of catalytic property; the durability of devices is decreased; and the fuel cost required for maintaining the reaction temperature is increased.

Method used

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  • Method of synthesizing higher-molecular alcohol
  • Method of synthesizing higher-molecular alcohol

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of Catalyst

[0044]A solution prepared by dissolving 225.2 g of calcium nitrate: Ca(NO3)2.4H2O in 5.0 liters of distilled water and a solution prepared by dissolving 78.87 g of ammonium phosphate: (NH4)2HPO4 in 3.0 liters of distilled water were added dropwise to aqueous ammonia of which pH had been adjusted to 9 to 11 under a nitrogen atmosphere, and the resultant mixture was stirred for one day. Subsequently, the mixture was filtrated, washed with water, and dried to obtain a powder. Ion-exchange water was added to the obtained powder, and the resultant mixture was crushed for 48 hours with a ball mill. The slip thus obtained was matured and dried at 140° C. in an oven. The resultant powder was calcinated in the air at 600° C. for 2 hours to obtain a powdery catalytic composition whose Ca / P molar ratio was 1.64.

example 2

Evaluation of Catalytic Property

[0045]A fixed bed gas flow catalytic reactor was used as a reactor. The powdery catalyst was formed into tablets of 14 to 26 mesh. The tablets were filled in a reaction tube in an amount in accordance with the contact time, and a thermal dehydration treatment was conducted as a pretreatment under carrier gas (1% Ar / He-based; flow 112 ml / min) atmosphere, at 500° C. for 30 minutes. After the pretreatment, the tablets were reacted at normal pressure under the conditions of ethanol concentration of 16 vol %, carrier gas flow 112 ml / min (total flow 134 ml / min).

[0046]In case of the high molecular alcohol synthesis experiment, the reaction temperature was fixed at 300° C., and the contact time was in a range of 0.02 to 29.4 seconds. In the optimization experiment of 1-butanol synthesis conditions, the contact time was fixed at 1.0 second, the ethanol concentration was 8.1%, and the reaction temperature was in a range of 150 to 500° C.

[0047]A gas chromatograp...

example 3

Example of Analysis by Gas Chromatography Mass Spectrometer (GC-MS)

[0054]The ethanol conversion experiment was conducted with the use of a hydroxyapatite catalyst at an ethanol concentration of 16%, for a contact time of 1.78 seconds and at a reaction temperature of 300° C., and an analysis was conducted with GC-MS. The results are shown in FIG. 3.

[0055]The peaks of 1-butanol, hexanol (2 types: iso and normal), octanol (2 types: iso and normal), and decanol (3 types: iso and normal) can be observed at the retention times of 8.5 minutes, 13 to 14 minutes, 17 to 18 minutes, and 20 to 22 minutes, respectively.

[0056]It can be seen from this result that high molecular alcohols having 4 or more and an even number of carbon atoms are synthesized selectively.

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Abstract

The present invention provides a production method with which high molecular alcohols having an even number of carbon atoms such as 1-butanol, hexanol, octanol and decanol, and a mixture of these are efficiently collected through clean processes with the use of ethanol as a raw material. High molecular alcohols are produced from ethanol by using calcium phosphate-based compounds such as hydroxyapatite Ca10(PO4)6(OH)2, tricalcium phosphate Ca3(PO4)2, calcium monohydrogen phosphate CaHPO4.(0˜2)H2O, calcium diphosphate Ca2P2O7, octacalcium phosphate Ca8H2(PO4)6.5H2O, tetracalcium phosphate Ca4(PO4)2O or amorphous calcium phosphate Ca3(PO4)2. nH2O as a catalyst, using ethanol as a starting material, and setting a contact time at 0.4 second or longer.

Description

INCORPORATION BY REFERENCE[0001]This application is a continuation-in-part application of international patent application Serial No. PCT / JP2005 / 022217 filed Dec. 2, 2005, which claims priority to Japanese patent application Serial No. JP 2004-351307 filed Dec. 3, 2004.[0002]The foregoing applications, and all documents cited therein or during their prosecution (“appln cited documents”) and all documents cited or referenced in the appln cited documents, and all documents cited or referenced herein (“herein cited documents”), and all documents cited or referenced in herein cited documents, together with any manufacturer's instructions, descriptions, product specifications, and product sheets for any products mentioned herein or in any document incorporated by reference herein, are hereby incorporated herein by reference, and may be employed in the practice of the invention.FIELD OF THE INVENTION[0003]The present invention relates to a method for producing high molecular alcohols from...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07C31/02
CPCC07C29/34C07C31/12C07C29/74
Inventor TSUCHIDA, TAKASHISAKUMA, SHUJI
Owner SANGI CO LTD
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